The overall objective of the total project is three-fold: 1) to synthesize Crotepoxide and its various isomers from unnatural starting materials and thus to confirm chemically the gross structure and the stereochemistry of these compounds; 2) to explore the stereochemistry and regiochemistry of allylic halogenation and allylic oxygenation of unsymmetrical olefins; and 3) to develop new methods for preparing epoxides and for converting epoxides into other useful functional groups. The key synthetic steps in the total synthesis involve (1) cis-hydroxylation of a symmetrical 1,4-cyclohexadiene, (2) allylic 1,4-dibromination of a substituted cyclohexane, (3) double epoxide formation from a bis-bromohydrin, and (4) stereoselective and regioselective trans-acetoxylation of a diepoxycyclohexene using the Prevost procedure. Exploration of allylic brominations and oxygenations are being carried out on model systems. A new method has been developed for conversion of epoxides into monoethers of 1,2-glycols (i.e., into 2-hydroxyethyl ethers , into 2-hydroxyethyl sulfides, and into 2-hydroxylethylamines under unusually mild conditions and even in the presence of many other normally reactive functional groups.